Vicinal diamines are very important functional moieties which are present in various biologically active compounds and have also been widely used as chiral control elements in asymmetric synthesis. Diamination of olefins presents an attractive strategy for the synthesis of vicinal diamines. While good progress has been made in this area, there are still important problems that remain unsolved. We propose to develop a catalytic diamination process involving diamido metal species to address some of these challenges. The long-term goal of the proposed research is to develop an efficient regio-, diastereo-, and enantioselective catalytic diamination method for olefins with broad scope and the ability to rationalize and predict the regio- and stereo-chemical outcome for a given olefin system. Development of such a method will eventually provide effective synthetic avenues to medicinally important compounds. The specific aims of the proposed research are: (1) to further understand and develop the Pd- and Cu(I)-catalyzed diamination through studies of reaction mechanism, expansion of substrate scope, and development of catalytic asymmetric processes; (2) to further explore other metal catalysts and nitrogen sources; (3) to explore the synthetic potential of the developed diamination method for the synthesis of useful building blocks and biologically active compounds.